When digging through the rubble of Helen's home, Brian and Casey unearth a suitcase and photograph that had been the Hackett brother's only inheritance from their late father. Brian's attempts to remind Joe of that fails, but Joe later sees a vision of his late father and forgives Brian. Meanwhile, Antonio takes his revenge on Brian and Casey and Helen takes out her anger on Casey's clothes.
A member of a wealthy family hires Joe and Brian to go to Miami to pick up the remains of the family patriarch, who died there. But because they drank a lot the night before they left, Joe got the wrong casket. So now they try to get the right one but there's going to be a viewing so what are they to do. Brian decides to let Joe take the dead man's place till the body arrives. And while waiting he learns all sorts of things about the man and his family.
Lowell witness a crime. The perp then tries to get him not to testify. The Feds then offer to place him in the Witness Protection Program but when he learns that if he does, he will no longer be able to see his friends. So he asks Joe what he should do but Joe tries to give him advice but tells him ultimately it's his decision.
When the insurance company gives Helen a big check for what she lost in the fire she goes on a shopping spree. Casey refuses to have sex with Brian unless they can find something they share in common. Antonio depressed at his (lack of a) love life decides to go back to his ex who is hideous.
When Brian starts eating incessantly and his work is affected, Joe tells him to get his act together. Helen tells him that he needs to go to her overeaters support group and when Brian goes to talk he reveals why he is eating so much. Antonio buys a pair of expensive shoes that are a little tight and he says he just has to break them in but it appears his feet are the ones that will break. Casey goes to interview for a job and pretends to be a fan of the Three Stooges which the man interviewing her is.
It's Christmas. Joe wants to bring Helen to Vermont but Helen wants to throw a traditional Christmas party. Joe agrees on the condition that as soon as it's over they go to Vermont. So Helen invites everyone and Brian tells Casey he's bringing a date because of what happened between them. She tells him she's also bringing a date, only it's a lie. She tries to find someone and picks Lewis. Things go bad when Joe learns that the road to Vermont will be closed in a few hours so he tries to rush the party. Antonio brings gifts for everyone, but they don't reciprocate so ...
Lyle, a man Fay met while on vacation comes to the island to court her. He proposes to her and they were in the process of getting married when the minister utters his full name. That's when Fay freaks out, because he has the same name as her other dead husbands. She then goes to Joe who is nursing a cold to ask him what she should do.
Joe and Brian decide to go to a hockey game in Boston. They ask Antonio to man the counter. He gives the last seat to an old woman. And then a guy who says he was booked to go on the flight arrives. But because he was late Antonio gave away the last seat. He says that he will regret it. Joe and Brian return and say the game was disappointing because the star player wasn't there. And Antonio tells them about the guy and they learn it was the hockey player. He later goes on the air and blames Sandpiper for missing the game. And that's when they're the most hated people ...
Helen learns that her ex boyfriend Davis has been detained in Asia for over a year and is now on his way back to see her. She then tells Joe to go to Boston to get something. The guys are wondering what's up with Helen. She tells them that she didn't break up with him when she accepted Joe's proposal. She tells them that on the night she was going to see Davis, Joe proposed to her and she accepted. She told Joe that she has to see him alone but when she sees him, he surprises her with a surprise engagement party. And before she could tell Davis she accepted Joe's ...
When Joe learns that Sandy Cooper (the woman he says is obsessed with him) is coming, he freaks out. Helen thinks he's out of his mind. And when she arrives, she's there for Brian. Joe goes on about how demented she is, Helen takes him to a therapist. But during one of his sessions Sandy shows up claiming to be his wife.
Antonio thinks his fortunes have taken a turn for the better, when one of his passengers hires him to a be his personal chauffeur. But some overheard conversations seem to indicate that his new boss is a mobster (he's actually a diamond broker). Meanwhile, Helen hurriedly reads "Don Quixote" when her old english lit teacher from highschool drops by for a visit.
Casey learns her job with the Tourism Board is hanging by a thread. But her boss informs her that he's going to give one of her ideas the go ahead and that is to get Nantucket a sister city. She finds one and the head, a Prince is coming with his wife to make it official. One of Brian's passengers, a woman comes on to him. The next day the Prince arrives and meets Casey. She asks where's the Princess and he says she came in the day before. When she arrives at the airfield to meet the Prince, Brian says she's the one he hooked up with. He then tells Casey about it and ...
After a chance encounter, Antonio searches for the girl he shared a moment with in the airport. He enlists everyone's help to try to find her. Brian and Helen size up women at the ticket counters for emotional baggage that they might carry.
Joe finds the time capsule, he, Brian, Helen and Casey buried when they were kids. Inside are letters that they wrote what they thought they would be in the future. So they each read their letter, Joe thought he would be baseball star, Brian thought he would be a spy, Casey thought she would be a supermodel. And they thought Helen would still be the fat girl And Helen is a musician.
Joe and Brian learn that a woman whom they know is an exotic dancer and will be performing for the last time so they decide to go. But Joe has to find a way not to tell Helen. But when she asks him where he is going, he makes up a story of volunteering at a retirement home. And in order to be able to look her in the eye he goes to the home.